Pentaketides and 5--Hydroxyphenyl-2-pyridone Derivative from the Culture Extract of a Marine Sponge-Associated Fungus KUFA0732.

Five undescribed pentaketide derivatives, ()-6,8-dihydroxy-4,5-dimethyl-3-methylidene-3,4-dihydro-1-2-benzopyran-1-one (), [(3,4)-3,8-dihydroxy-6-methoxy-4,5-dimethyl-1-oxo-3,4-dihydro-1-isochromen-3-yl]methyl acetate (), ()-5, 7-dimethoxy-3-((-(1-hydroxyethyl)-3,4-dimethylisobenzofuran-1(3)-one (), ()-7-hydroxy-3-(()-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran 1(3)-one (), and a -hydroxyphenyl-2-pyridone derivative, avellaneanone (), were isolated together with the previously reported ()-3-acetyl-7-hydroxy-5-methoxy-3,4-dimethylisobenzofuran-1(3)-one (), ()-7-hydroxy-3-(()-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3)-one () and isosclerone (), from the ethyl acetate extract of a culture of a marine sponge-derived fungus, KUFA0732. The structures of the undescribed compounds were elucidated using 1D and 2D NMR, as well as high-resolution mass spectral analyses. The absolute configurations of the stereogenic carbons in , , , and were established by X-ray crystallographic analysis.

New Hybrid Phenalenone Dimer, Highly Conjugated Dihydroxylated C Steroid and Azaphilone from the Culture Extract of a Marine Sponge-Associated Fungus, KUFA 1767.

An undescribed hybrid phenalenone dimer, talaropinophilone (), an unreported azaphilone, 7--pinazaphilone B (), an unreported phthalide dimer, talaropinophilide (), and an undescribed 9,15-dihydroxy-ergosta-4,6,8 (14)-tetraen-3-one () were isolated together with the previously reported bacillisporins A () and B (), an azaphilone derivative, Sch 1385568 (), 1-deoxyrubralactone (), acetylquestinol (), piniterpenoid D () and 3,5-dihydroxy-4-methylphthalaldehydic acid () from the ethyl acetate extract of the culture of a marine sponge-derived fungus, KUFA 1767. The structures of the undescribed compounds were elucidated by 1D and 2D NMR as well as high-resolution mass spectral analyses. The absolute configuration of C-9' of and was revised to be 9' using the coupling constant value between C-8' and C-9' and was confirmed by ROESY correlations in the case of .

New Alkylpyridinium Anthraquinone, Isocoumarin, C-Glucosyl Resorcinol Derivative and Prenylated Pyranoxanthones from the Culture of a Marine Sponge-Associated Fungus, KUFA 2017.

An unreported isocoumarin, (,4)-4-hydroxy-6-methoxymellein (), an undescribed propylpyridinium anthraquinone (), and an unreported C-glucosyl resorcinol derivative, acetyl carnemycin E (), were isolated, together with eight previously reported metabolites including -hydroxybenzaldehyde (), 1,3-dimethoxy-8-hydroxy-6-methylanthraquinone (), 1,3-dimethoxy-2,8-dihydroxy-6-methylanthraquinone (), emodin (), 5[(3,5)-nona-3,5-dien-1-yl]benzene (), carnemycin E (), tajixanthone hydrate () and 15-acetyl tajixanthone hydrate (), from the ethyl acetate extract of the culture of a marine sponge-derived fungus, KUFA 2017. The structures of the undescribed compounds were elucidated by 1D and 2D NMR and high resolution mass spectral analyses. In the case of , the absolute configurations of the stereogenic carbons were determined by comparison of their calculated and experimental electronic circular dichroism (ECD) spectra.

Prenylated phenylbutyrolactones from cultures of a marine sponge-associated fungus Aspergillus flavipes KUFA1152.

Four undescribed prenylated phenylbutyrolactones, aspulvinones R, S, T and U, were isolated together with the previously reported aspulvinones A, B', H and 4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzaldehyde, from cultures of the marine sponge-derived fungus Aspergillus flavipes KUFA1152. The structures of the undescribed compounds were established on the basis of extensive analysis of 1D and 2D NMR and HRMS spectra. In the case of aspulvinone T, the absolute configuration of its stereogenic carbon was established by comparison of the experimental and calculated electronic circular dichroism (ECD) spectra.